20 answers
Dinso
Student
Burtonsville, Maryland
1
Question
Updated
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What was the most unexpected challenge you faced while pursuing your career, and how did you handle it?
College Sophomore preparing to transfer to a 4 year in the Fall
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19 answers
Citi Volunteers
137
Answers
New York, New York
Updated
Citi’s Answer
The early start of my career I was blessed to be in a stable role with growth in a well knit organization for a good length of time. Overall a positive and thriving culture.
Then unexpectedly there was a major challenge and failure at our organization and many rapid changes in leadership and leadership style. Some very confrontational and inter office politics made work very challenging.
I had to reassess and reevaluate the working style both for my team and myself. Making objective decisions, leaving emotions off. Teaching both my team and myself to navigate the change in environment.
I eventually left as it was not the best environment, however this also became a huge learning experience to handle confrontation and conflict management in a more positive manner.
Then unexpectedly there was a major challenge and failure at our organization and many rapid changes in leadership and leadership style. Some very confrontational and inter office politics made work very challenging.
I had to reassess and reevaluate the working style both for my team and myself. Making objective decisions, leaving emotions off. Teaching both my team and myself to navigate the change in environment.
I eventually left as it was not the best environment, however this also became a huge learning experience to handle confrontation and conflict management in a more positive manner.
Avondra Grimes
Customer Care
4
Answers
Bryan, Texas
Updated
Avondra’s Answer
During my college years, the hardest experience I faced was losing someone very important to me in my sophomore year. It was difficult to stay motivated and focused after that loss. My best advice is to take life one day at a time and be kind to yourself. Life will bring unexpected challenges, so always remember who you are and what you want to achieve. Also, find a healthy balance between work and enjoyment, and celebrate the small victories.
Citi Volunteers
137
Answers
New York, New York
Updated
Citi’s Answer
- There were many challenges throughout my career. Best way to handle challenges is to deal with it and to stay strong. You always learn from every challenge and come out stronger.
- I worked in publishing and at the time publications were moving away from print to digital and I needed new skills given the shift to digital so I started to take digital courses and look for a job where it was more digital than print.
- The biggest challenge was transitioning from a setting that was somewhat flexible to a more structured weekly schedule and being able to balance work-life priorities.
- Being different - thinking that I was different and I needed to re-group my skills and culture.
- I worked in publishing and at the time publications were moving away from print to digital and I needed new skills given the shift to digital so I started to take digital courses and look for a job where it was more digital than print.
- The biggest challenge was transitioning from a setting that was somewhat flexible to a more structured weekly schedule and being able to balance work-life priorities.
- Being different - thinking that I was different and I needed to re-group my skills and culture.
Citi Volunteers
137
Answers
New York, New York
Updated
Citi’s Answer
- I think early on I didn’t realize how important it was to build relationships with my colleagues. Once I realized that and thought of colleagues as friends it really changed my perspective and had a really positive impact on our work products.
- I am still working on balancing having a family and growing professionally. It is a daily pursuit, where everyday I ask myself, "have I done everything I can to serve both my family and my career?" The demands for both fluctuate, and I am focused on doing both to the best of my ability on any given day.
- Losing my job was difficult early in my career. I relied on my network of family, friends and colleagues to help land my next role.
- I am still working on balancing having a family and growing professionally. It is a daily pursuit, where everyday I ask myself, "have I done everything I can to serve both my family and my career?" The demands for both fluctuate, and I am focused on doing both to the best of my ability on any given day.
- Losing my job was difficult early in my career. I relied on my network of family, friends and colleagues to help land my next role.
Citi Volunteers
137
Answers
New York, New York
Updated
Citi’s Answer
- Imposter syndrome when I got a big promotion. I had applied for the promotion and felt very confident in my abilities to succeed in this new role during the interview process, but when I actually started in the new role I lost my confidence and felt overwhelmed that I had taken on too much too soon. After some days/weeks of increasing panic and insecurity, I discussed this with my manager, a therapist and friends and family and they helped me get through this period of imposter syndrome to ultimately succeed in the role and beyond.
- As someone who did not know what they wanted to do when applying for my first job out of school, it was daunting to “tell my story” and figure out how to be impactful in my role. I found that constantly being curious, being innovative and entrepreneurial, and making meaningful connections with my colleagues was the most helpful thing to overcome this.
- As someone who did not know what they wanted to do when applying for my first job out of school, it was daunting to “tell my story” and figure out how to be impactful in my role. I found that constantly being curious, being innovative and entrepreneurial, and making meaningful connections with my colleagues was the most helpful thing to overcome this.
Citi Volunteers
137
Answers
New York, New York
Updated
Citi’s Answer
- Communication with unknowledgeable client. Needed to explain more easy verbiage and presentation. Ability to explain easy word means you can understand it thoroughly.
- Corporate life comes with ups and downs. A challenge I faced was dealing with a reorganization of my team and having to figure out what to do next.
- During my first rotation, that team got layoff and I had to navigate starting all over. I adapted very quickly and with the help of my sponsors and mentors, I was able to make a smooth transition to another team which I quickly had to learn the business and keep pushing forward. I learned that as a young analyst, you have to be adaptable and curious in order to be successful.
- Corporate life comes with ups and downs. A challenge I faced was dealing with a reorganization of my team and having to figure out what to do next.
- During my first rotation, that team got layoff and I had to navigate starting all over. I adapted very quickly and with the help of my sponsors and mentors, I was able to make a smooth transition to another team which I quickly had to learn the business and keep pushing forward. I learned that as a young analyst, you have to be adaptable and curious in order to be successful.
Citi Volunteers
137
Answers
New York, New York
Updated
Citi’s Answer
- Getting comfortable with rejection. You need to comfortable with the idea of hearing “no”, from jobs or other opportunities. However, you need to get comfortable with putting yourself out there and vocalizing your goals. You never know when you’ll hear a “yes” and there are worse things than hearing “no”. A rejection doesn’t stop you from achieving your goals, just an opportunity to work harder or pivot plans. You never know until you ask and a “no” doesn’t change anything!
- After entering the workforce following college, I was laid off from my first position after just one year. At the time, it was a difficult and humbling experience, but it taught me an important lesson: setbacks do not define your future—how you respond to them does. Rather than viewing it as a failure, I used it as an opportunity to reflect on my strengths, reassess my career goals, and identify where I could make the greatest impact. That experience ultimately helped me find a clearer direction and motivated me to invest in my growth, positioning myself for opportunities where I could thrive and succeed.
- After entering the workforce following college, I was laid off from my first position after just one year. At the time, it was a difficult and humbling experience, but it taught me an important lesson: setbacks do not define your future—how you respond to them does. Rather than viewing it as a failure, I used it as an opportunity to reflect on my strengths, reassess my career goals, and identify where I could make the greatest impact. That experience ultimately helped me find a clearer direction and motivated me to invest in my growth, positioning myself for opportunities where I could thrive and succeed.
Citi Volunteers
137
Answers
New York, New York
Updated
Citi’s Answer
- To be blunt, it’s hard to break into a prestigious corner of the field unless you have a top tier degree, connections, or an internship. It’s a very competitive field. So in my case, it took some pivoting from the Insurance sector to consulting in the Insurance/Financial Services space to build translatable skills and find my way into the internal consulting role at Citi I find myself in today.
- Moving to a different country for personal reasons and try to find a job in the new destination. I had to first learn the professional protocols and culture and how to find a job in the new country.
- Understanding that your path will differ from your peers - there is no “correct” way to go about your career journey and every step you take develops new skills.
- Moving to a different country for personal reasons and try to find a job in the new destination. I had to first learn the professional protocols and culture and how to find a job in the new country.
- Understanding that your path will differ from your peers - there is no “correct” way to go about your career journey and every step you take develops new skills.
Jenny khew
1
Answer
Singapore
Updated
Jenny’s Answer
During early part of my career, whenever I face with uncontrollable factors that are impacting my work, I get agitated easily. Like when you expect email response from others within reasonable timeframe or issue resolution within stipulated time (professionalism), unwillingness of others to share more knowledge or answers etc (sometimes gatekeeper). Across the years, i'd learnt to stay calm (take a short break, walk away from the PC for a while), be more compassionate (perhaps we have different work priority thus the matter had not been looked into yet etc), and stay positive and be resilient. You will get there surely!
Citi Volunteers
137
Answers
New York, New York
Updated
Citi’s Answer
- One of the most unexpected challenges I faced was navigating organizational changes and a layoff a few years into my job. It was a difficult experience because it forced me to adapt quickly and reassess my next steps. I handled it by focusing on what I could control—continuing to develop my skills, networking, and staying open to new opportunities. Looking back, it taught me resilience and reinforced the importance of being adaptable in a constantly changing industry.
- Nothing is worse than looking for your first job as an international student during financial crisis. There were very limited job openings, and most of those were only open to U.S. residents. The way how I handled was telling myself not to be bothered by the things out of my control. I continued learning and practicing my interview skills while looking for jobs. Be more open to explore different areas and industries. Expand network and connect to people. Start with small project or job to show that what you can do.
- Nothing is worse than looking for your first job as an international student during financial crisis. There were very limited job openings, and most of those were only open to U.S. residents. The way how I handled was telling myself not to be bothered by the things out of my control. I continued learning and practicing my interview skills while looking for jobs. Be more open to explore different areas and industries. Expand network and connect to people. Start with small project or job to show that what you can do.
Citi Volunteers
137
Answers
New York, New York
Updated
Citi’s Answer
- The most unexpected challenge I faced: I started at Saloman Brothers in 1997 one month before they merged with Smith Barney. I had to navigate the change as the last person hired. Hard work and dedication to the changes with the merge led to a 29 year career at Citi. A good trait to go with the flow. You are on the journey you are meant to be on even when circumstances change and challenges pop up.
- I moved from London to New York through working at Morgan Stanley at the time. Although there were a lot of similarities between the UK and the US there were also many differences. The culture is different. I also wanted to learn about all the different sports here like American football, basketball and baseball. I found the best approach was to have an open mind and be willing to experiencing different things.
- I moved from London to New York through working at Morgan Stanley at the time. Although there were a lot of similarities between the UK and the US there were also many differences. The culture is different. I also wanted to learn about all the different sports here like American football, basketball and baseball. I found the best approach was to have an open mind and be willing to experiencing different things.
Citi Volunteers
137
Answers
New York, New York
Updated
Citi’s Answer
- I think the most unexpected challenge was being thrown into situations where i needed to cover more than one role at a time. As team members come and go from the company, it is inevitable that you will need to cover someone's work in addition to your own at some point. Handling two roles at once required me to be very patient with myself, and also actively manage expectations of those counting on me in each of the roles. I am only human and doing my best, so i needed to lay out expectations for all so that everything was out in the open.
- Finding a role that aligned with my interests was pretty difficult, especially when beginning my career. The best way to handle that is to recognize what you know vs what you don’t know. Then, articulate what you’ve done to the best of your ability and relate it to the role you’re pursuing. Anything you may not know for the role you should do your research on - even if you incorrectly cite info or facts about a topic, it displays intuition and will help secure the role.
- Finding a role that aligned with my interests was pretty difficult, especially when beginning my career. The best way to handle that is to recognize what you know vs what you don’t know. Then, articulate what you’ve done to the best of your ability and relate it to the role you’re pursuing. Anything you may not know for the role you should do your research on - even if you incorrectly cite info or facts about a topic, it displays intuition and will help secure the role.
Citi Volunteers
137
Answers
New York, New York
Updated
Citi’s Answer
- COVID made me realize I wasn't happy with my job at the time. Don't wait for a catastrophe to make a change!
- The challenge of not knowing where my career is headed after graduation. I interned at an opportunity I didn’t love and I knew that I couldn’t come back full time to do something I didn’t like. So the challenge of navigating the unknown and recreating what I want to do and who I want to be was hard. I learned to let go and accept my passions. Tried to not look at my peers and only make myself the competition I need to compete against.
- Most unexpected challenge was when I changed industry from healthcare to banking. At first I thought I made a wrong choice, however with time I started engaging more with Internal stakeholders to learn and understand the Banking industry. Now I am getting there. Its ok to fail as long as we are trying and learning.
- The challenge of not knowing where my career is headed after graduation. I interned at an opportunity I didn’t love and I knew that I couldn’t come back full time to do something I didn’t like. So the challenge of navigating the unknown and recreating what I want to do and who I want to be was hard. I learned to let go and accept my passions. Tried to not look at my peers and only make myself the competition I need to compete against.
- Most unexpected challenge was when I changed industry from healthcare to banking. At first I thought I made a wrong choice, however with time I started engaging more with Internal stakeholders to learn and understand the Banking industry. Now I am getting there. Its ok to fail as long as we are trying and learning.
Citi Volunteers
137
Answers
New York, New York
Updated
Citi’s Answer
- I was initially told that without an MBA degree I couldn’t join that I was looking to be a part of. I was persistent as there had to be other roles in the team that didn’t require an MBA, be curious and open to the unexpected path. It took me longer to get to where I wanted to be without the MBA, but I made it happen.
- Resuming work during COVID times after maternity leave. I was able to hone on my organizational skills to balance the unknowns
- Feeling like an imposter doing things that I didn’t know how to initially. I had to learn to overcome the fear of not being good enough and just do my best, fail sometimes, and learn each day until I felt more comfortable and confident.
- Resuming work during COVID times after maternity leave. I was able to hone on my organizational skills to balance the unknowns
- Feeling like an imposter doing things that I didn’t know how to initially. I had to learn to overcome the fear of not being good enough and just do my best, fail sometimes, and learn each day until I felt more comfortable and confident.
Richa Sachdeva
Recruiting Advisor
5
Answers
India
Updated
Richa’s Answer
At the beginning of my career, I found it challenging to work with different types of people and adapt to their styles and behaviors. I often struggled to understand what others expected or thought, which made me feel lost. However, I stayed positive and persevered, focusing on doing my best work. As I improved, dealing with difficult people and situations became easier. I learned to respond thoughtfully instead of reacting, which helped me understand others better. If you stay good at what you do and have patience and resilience, these challenges won't last. Keep practicing positive thinking and maintain a forward-looking approach in life.
B K
Digital Marketing
5
Answers
Singapore
Updated
B’s Answer
Hey Dinso,
I can't remember my most unexpected challenge as there are many and its part and parcel. My advice on how to handle it is to have an open mind. Growth comes in many ways and having unexpected challenges is one of the best ways to have significant growth.
As the saying goes "A smooth sea never made a skilled sailor".
All the best in your journey!
I can't remember my most unexpected challenge as there are many and its part and parcel. My advice on how to handle it is to have an open mind. Growth comes in many ways and having unexpected challenges is one of the best ways to have significant growth.
As the saying goes "A smooth sea never made a skilled sailor".
All the best in your journey!
Eesha Srivatsavaya
Consulting
6
Answers
McLean, Virginia
Updated
Eesha’s Answer
I found it most challenging how a lot of the skills you need for your job aren't directly taught in school. I learned a lot of things along the way post-grad. It's good to be a life-long learner
Lihan Wang
Marketing
2
Answers
Taipei, Taiwan
Updated
Lihan’s Answer
There will come a time when you realize that what you were once so passionate about has turned into something else. When that moment comes, don’t panic—pause, breathe, and allow yourself to reset your expectations.
Desislava Nikolova
Executive Assistant
4
Answers
Sofia, Bulgaria
Updated
Desislava’s Answer
What I found most challenging in my career so far was to accept that people and perceptions are different and that's the most normal thing. In professional life it's improtant to remember that nothing is personal and constructive feedback is required if you wish to improve and growth. You can achive that by asking questions proactively and seek confirmation of common understanding of goals/objectives.